Garland was selected with the fifth overall pick in the 2019 NBA Draft by the Cavaliers. He made his NBA debut during the first game of the season, Oct. 23 against the Magic. Garland played 32 minutes and recorded eight points (3-9 FG, 2-4 3Pt), five assists, two rebounds and one steal. In his 59 appearances, Garland averaged 12.3 points, 3.9 assists and 1.9 rebounds in 30.9 minutes. He shot 40.1 percent from the field, hit 1.8 threes at 35.5 percent and shot 87.5 percent from the free-throw line. Garland set single-game career highs of 23 points, 10 assists, five rebounds, three steals and one block. His longest streak of double-digit scoring was 15 games from Dec. 28 through Jan. 25. Across that stretch, Garland averaged 14.9 points on 13.7 shots, 4.9 assists, 1.7 rebounds and 1.0 steals in 34.4 minutes. He recorded his only double-double Jan. 14 against the Clippers. That included 14 points (5-16 FG, 2-7 3Pt, 2-2 FT), 10 assists and one steal in 28 minutes.